Methyl iodide → 5-fluoro-1-methyl-1H-indole-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

In DMF (100 ml) was dissolved 5-fluoroindol-3-carbaldehyde (5.17 g, 36.7 mmol). To the resulting solution was added sodium hydride (60% in oil, 1.39 g, 34.9 mmol) in portions under stirring at 0° C. After the reaction mixture was stirred at the same temperature for 1 hour, methyl iodide (4.57 ml, 73.4 mmol) was added thereto at 0° C. The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was poured in 1N HCl, followed by extraction with ether. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was crystallized by adding thereto chloroform/hexane. The crystals thus precipitated were collected by filtration under reduced pressure and dried under reduced pressure to give 5-fluoro-1-methylindole-3-carbaldehyde (2.53 g, 39%) as a white crystalline powder.

Provenance & Evidence